5428-02-4

Basic information

• Product Name: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL
• Synonyms: 2-NITRO-2-PHENYL-1,3-PROPANEDIOL;2-NITRO-2-PHENYLPROPANE-1,3-DIOL;AURORA KA-563;Nitodiol
• CAS NO: 5428-02-4
• Molecular Formula: C₉H₁₁NO₄
• Molecular Weight: 197.19
• EINECS: 410-360-4
• Product Categories: Propanes/propenes
• Mol File: 5428-02-4.mol
• Article Data: 9

Chemical Properties

• Melting Point: 100-102°C
• Boiling Point: 396 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: /
• Density: 1.337 g/cm³
• Vapor Pressure: 5.56E-07mmHg at 25°C
• Refractive Index: 1.58
• PKA: 12.53±0.10(Predicted)
• CAS DataBase Reference: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(5428-02-4)
• EPA Substance Registry System: 2-NITRO-2-PHENYLPROPANE-1,3-DIOL(5428-02-4)

Safety Data

• Hazard Codes: T,N
• Statements: 21/22-39-41-43-51/53-48/25
• Safety Statements: 45-53-61
• RIDADR: 3077
• HazardClass: IRRITANT
• Hazardous Substances Data: 5428-02-4(Hazardous Substances Data)

Usage

General Description

2-NITRO-2-PHENYLPROPANE-1,3-DIOL, also known as p-nitrophenyldiphenylpropane-1,3-diol, is a chemical compound with the molecular formula C15H15NO4. It is a nitrophenyl derivative of diphenylpropane-1,3-diol and is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds. 2-NITRO-2-PHENYLPROPANE-1,3-DIOL is notable for its nitro group, which imparts reactivity and unique chemical properties. It is also used as a starting material for the synthesis of various organic compounds and has potential applications in the field of medicinal chemistry and drug development. Additionally, it is important to handle 2-NITRO-2-PHENYLPROPANE-1,3-DIOL with care, as it may pose health and safety hazards if not used properly.

InChI:InChI=1/C9H11NO4/c11-6-9(7-12,10(13)14)8-4-2-1-3-5-8/h1-5,11-12H,6-7H2

Upstream product

• 50-00-0 formaldehyd 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 622-42-4 1-nitro-1-phenylmethane 
• 121-44-8 triethylamine 

Downstream Products

• 5428-03-5 2-amino-2-phenyl-propane-1,3-diol 
• 873975-55-4 1,3-dimethyl-5-nitro-5-phenyl-hexahydro-pyrimidine 
• 90918-76-6 5-nitro-5-phenyl-[1,3]oxazinane 
• 97260-34-9 5-nitro-2,5-diphenyl-[1,3,2]dioxaborinane 
• 37561-37-8 2,2-dimethyl-5-nitro-5-phenyl[1,3]dioxane 
• 861198-44-9 2,2-dimethyl-5-nitrone-N-(2-methyl-1-propene)-5-phenyl[1,3]dioxane 
• 861198-45-0 2,2-dimethyl-5-nitroxide-N-(2-methyl-1-phenylpropyl)-5-phenyl[1,3]dioxane 
• 861198-46-1 N-(2,2-dimethyl-5-phenyl[1,3]dioxan-5-yl)-N-(2-methyl-1-phenylpropyl)-O-(1-phenylethyl)hydroxylamine 
• 92959-70-1 3-acetyl-5-nitro-5-phenyl-[1,3]oxazinane 
• 93332-71-9 5-nitro-3-(4-nitro-benzoyl)-5-phenyl-[1,3]oxazinane 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 37561-42-5 2,2-dimethyl-5-phenyl-1,3-dioxan-5-amine 

Relevant articles and documents

Broadening antifungal spectrum and improving metabolic stablity based on a scaffold strategy: Design, synthesis, and evaluation of novel 4-phenyl-4,5-dihydrooxazole derivatives as potent fungistatic and fungicidal reagents

5-phenylthiophene derivatives exhibited excellent antifungal activity against Candida albicans, Candida tropicalis and Cryptococcus neoformans. However, optimal compound 7 was inactive against Aspergillus fumigatus and unstable in human liver microsomes in vitro with a half-life of 18.6 min. To discover antifungal agents with a broad spectrum and improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of 4-phenyl-4,5-dihydrooxazole derivatives were designed and synthesized. It was especially encouraging that compound 22a displayed significant antifungal activities against eight susceptible strains and seven FLC-resistant strains. Furthermore, the potent compound 22a could prevent the formation of fungalbiofilms and displayed satisfactory fungicidal activity. In addition, the metabolic stability of compound 22a was improved significantly, with the half-life of 70.5 min. Compound 22a was almost nontoxic to mammalian A549, MCF-7, HepG2, and 293T cells. Moreover, pharmacokinetic studies in SD rats showed that compound 22a exhibited pharmacokinetic properties with a bioavailability of 15.22% and a half-life of 4.44 h, indicating that compound 22a is worthy of further study.

Improving the metabolic stability of antifungal compounds based on a scaffold hopping strategy: Design, synthesis, and structure-activity relationship studies of dihydrooxazole derivatives

L-amino alcohol derivatives exhibited high antifungal activity, but the metabolic stability of human liver microsomes in vitro was poor, and the half-life of optimal compound 5 was less than 5 min. To improve the metabolic properties of the compounds, the scaffold hopping strategy was adopted and a series of antifungal compounds with a dihydrooxazole scaffold was designed and synthesized. Compounds A33-A38 substituted with 4-phenyl group on dihydrooxazole ring exhibited excellent antifungal activities against C. albicans, C. tropicalis and C. krusei, with MIC values in the range of 0.03–0.25 μg/mL. In addition, the metabolic stability of compounds A33 and A34 in human liver microsomes in vitro was improved significantly, with the half-life greater than 145 min and the half-life of 59.1 min, respectively. Moreover, pharmacokinetic studies in SD rats showed that A33 exhibited favourable pharmacokinetic properties, with a bioavailability of 77.69%, and half-life (intravenous administration) of 9.35 h, indicating that A33 is worthy of further study.

2, 4, 4-trisubstituted dihydrooxazole derivative and application thereof

The invention belongs to the technical field of drug synthesis, and relates to 2, 4, 4-trisubstituted dihydrooxazole derivatives, pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, preparation methods of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, and an application of the 2, 4, 4-trisubstituted dihydrooxazole derivatives and the prodrugs thereof as drugs for treating various diseases caused by fungal infection. The general formula of the 2, 4, 4-trisubstituted dihydrooxazole derivative and the stereoisomer or the pharmaceutically acceptable salt, hydrate, solvate or prodrug thereof is shown as (I), wherein MBG, X, Y, M and R1 are shown in the claims and the specification. .